Luxury Vacation Rentals on Anna Maria Island
Anna Maria Island offers a serene escape with its white sandy beaches, crystal-clear waters, and relaxed, laid-back atmosphere. Our luxury vacation rentals on the island provide a perfect home away from home, whether you're seeking a cozy beachfront cottage, an elegant villa, or a spacious family-friendly retreat. Each property is carefully designed to offer comfort and convenience, with easy access to Anna Maria Island’s best attractions. Experience the beauty of Anna Maria Island and create lasting memories with Once Upon A Beach’s exceptional vacation homes. Immerse yourself in the ultimate island lifestyle with our premier rentals.
Looking to accommodate a specific number of guests? You can also browse our listing of luxury vacation rentals by bedroom: 2 Bedrooms, 3 Bedrooms, 4 Bedrooms, and 5+ Bedrooms.
At Once Upon a Beach, we treat every home as if it were our own and every guest like family. When you book your next vacation with us, you'll receive unparalleled service and a stress-free experience from our team of Anna Maria Island locals and experts. We're proud to be locally-owned and operated, and to provide you with a boutique and intimate style of care. We'd love to help you find your next vacation rental today!
40 properties available
Welcome to Island Girl East!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Island Girl East*Island Girl East offers a luxurious and spacious retreat near Holmes Beach with room for up to 5 guests, featuring decks, a gourmet kitchen, a shared heated pool, and easy access to Anna Mar
Welcome to Sea La Vie Beach House!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.A luxurious 2,825 sq. ft. canal-front home featuring a heated pool, spa, and spacious living areas designed for relaxation and comfort.HIGHLIGHTS: Open Concept Living:&nbs
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Newly Built Luxury Canal-Front Home with Pool, Spa, and Private DockHIGHLIGHTS: Private Single-Family Home: Unique and spacious layout, professionally designed for comfort and luxu
Welcome to Sea La Vie!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Discover the ultimate in luxury island living at Sea La Vie, a custom-built retreat located on the desirable north end of Anna Maria Island. With 2,933 sq. ft. of elegant living space
Welcome to Three Little Birds!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Luxury Waterfront Living with Gulf Views, Heated Pool, and Island CharmHIGHLIGHTS: Spacious and Open Layout: Living, dining, and kitchen areas designed for seamless gathe
Welcome to The Oasis at Palmetto!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience unparalleled relaxation at this coastal chic retreat, just steps from direct beach access to the pristine Gulf of Mexico. This stunning 4-bedroom, 3.5-bathroom h
Welcome to Sunsets on Carissa!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated vacation rental agency.A Stunning Beachside Escape with a Private Heated Pool, Game Room, and Gulf BreezesHIGHLIGHTS: Open Layout: Bright and airy kitchen, dining, and living area with a large TV, per
Welcome to Family Tides – Unit B!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation Rentals*This listing is for ONE unit; Family Tides B*Family Tides – Unit B is a bright and spacious second-floor condo that offers 3 bedrooms, 2 bathrooms, and access to shared outdoor amenities, including a he
Welcome to Serenity Now!On Anna Maria Island (Holmes Beach, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Peace and Paradise at Serenity Now – Your Dream Vacation Home on Anna Maria IslandHIGHLIGHTS: Spacious Open Layout: Enjoy a bright, airy kitchen, dining, and
Welcome to Ocean Sunrise!On Anna Maria Island (Bradenton Beach, FL)Managed by Once Upon A Beach Vacation RentalsUnmatched Luxury Featuring a Private Dock, Heated Pool, Putting Green, Game Room, and Spacious Accommodations for an Unforgettable Beachside EscapeHIGHLIGHTS: 4,793 sq. ft. of luxurious living space Prime Bayfront location with
Welcome to AMI Peppertree Paradise!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Enjoy a sun-soaked getaway at AMI Peppertree Paradise, where comfort, convenience, and island charm come together for the perfect Anna Maria Island vacation rental!1970 s
Welcome to Casa Mariposa!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience the charm and luxury of Casa Mariposa, a hidden gem that combines 'Old-Florida' elegance with modern amenities. Nestled behind lush gardens and a butte
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